Diethyl Oxalate → HCID 15337214, compound

HRID 1439903Notes

Reaction equation

HRID 1439903 reaction equation
CC(C)([O-])C.[K+].[C:7]([O:14][CH2:15][CH3:16])(=[O:13])[C:8]([O:10]CC)=O.[Cl:17][C:18]1[CH:27]=[C:26]2[C:21]([CH2:22][CH2:23][CH2:24][CH2:25]2)=[C:20]([N+:28]([O-:30])=[O:29])[CH:19]=1.OS([O-])(=O)=O.[K+]>C(O)C>[Cl:17][C:18]1[CH:27]=[C:26]2[C:21](=[C:20]([N+:28]([O-:30])=[O:29])[CH:19]=1)[CH:22]([C:8]([C:7]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])[CH2:23][CH2:24][CH2:25]2

Participants

6

Reactant 4

HCID 7268Diethyl OxalateHCID 516920Potassium bisulfateHCID 18984759HCID 18984759, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15337214HCID 15337214, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of potassium t-butoxide (79.49 g, 0.708 mol) and diethyl oxalate (105.8 mL, 0.779 mol) in ethanol (140 mL) was added 7-chloro-5-nitrotetralin (14 g, 0.071 mol) at room temperature. The mixture was stirred for 2 h, poured into 10% aqueous KHSO4, and extracted with ethyl acetate (400 mL×2). The combined organic layers were washed successively with water and brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 15:1~6:1 hexane/-ethyl acetate to give 8.39 g of the title compound: 1H NMR (CDCl3) δ7.91 (d, 1H, J=2.1 Hz), 7.45 (d, 1H, J=6.3, 4.0 Hz), 4.41 (m, 2H), 2.82~3.09 (m, 2H), 2.02 (m, 2H), 1.85 (m, 2H), 1.42 (t, 3H, J=7.3 Hz).

Workup

  1. extractionextracted with ethyl acetate (400 mL×2)
  2. washThe combined organic layers were washed successively with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography with 15:1~6:1 hexane/-ethyl acetate

Sources & evidence

ORD record
ord-6b6c6eda683f463587e86fc4a8982599
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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